A facile synthesis of an aldehydic analog of platelet activating factor and its use in the production of specific antibodies.
The multistep synthesis of a platelet activating factor (PAF) analog having a reactive aldehyde group at the omega-end of the sn-1 position is described. A novel ozonolysis of a double bond was employed to generate the aldehyde group in high yield under mild conditions. The aldehyde group was generated at the last step of the synthesis to avoid any reactions of protection and deprotection. The natural chiral center at the sn-2 position was introduced at the first step so that no steric resolution of the final product was needed. This analog of PAF was conjugated to thyroglobulin via reductive amination and then used to immunize rabbits for production of specific antibodies. The purified antibodies bind stereospecifically to tritiated PAF and crossreact minimally with lyso-PAF, plasmalogens and other phospholipids. The solid-phase radioimmunoassay thus developed detects as low as 20 pg of PAF per assay tube and should be applicable to the quantitation of PAF in biological systems.
Wang
C J
CJ
Division of Medicinal Chemistry and Pharmaceutics, College of Pharmacy, University of Kentucky, Lexington 40536-0082.
Tai
H H
HH
D000447:Aldehydes / Q000138:chemical synthesis* / Q000276:immunology; D000818:Animals; D000906:Antibodies; D000917:Antibody Formation; D000918:Antibody Specificity; D002417:Cattle; D005260:Female; D010972:Platelet Activating Factor / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000276:immunology; D011817:Rabbits; D011863:Radioimmunoassay / Q000379:methods; D013954:Thyroglobulin / Q000138:chemical synthesis / Q000276:immunology
D000447:Aldehydes; D000906:Antibodies; D010972:Platelet Activating Factor; D013954:Thyroglobulin